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George Clooney opens up about politics, life at 50, and what he’s learned from failure in this Sunday’s PARADE with David Gergen. In the exclusive extras below, the star talks about his infamous pranks and his early years in Hollywood.

On playing pranks “You set a bit of a trap and then you watch it slowly unfold. I’ve had ones that have taken years. I took a painting out of the trash once, and I put it up on an easel in my house and got some paints, and I convinced one of my best friends, [actor] Richard Kind, that I was painting. I bought some other pictures, I told him I was studying art. And then for his 40th birthday I gave him this horrible painting. He had to hang it on his wall, [it was by] his best friend! And for years people would come over—everyone else knew it was out of the trash—and go, ‘That is a beautiful painting.’ [Laughs] And he was convinced by the end that it was a beautiful painting. Until I did The Tonight Show, I think, and told the story and then I told him to watch the show. And he said, ‘I hate that painting.’

“There’s good fun in watching those play out. And, hey, my friends are rough on me too. Brad Pitt‘s brutal, and Matt Damon. My friends used to change my outgoing phone message all the time. This was the old days, when you had a phone machine. They would change the message to something horrible and there was nothing I could do to change it back. That was always brilliant.”

On making the move to Hollywood “The summer I was 21 I was cutting tobacco in Kentucky for a living, making $3 an hour. That’s when you decide you’ve got to move to Hollywood. [Laughs] My cousin Miguel Ferrer and his father, Jose Ferrer, came to Kentucky to do a movie and they got me a job as an extra, at $20 a day, which is good money when you’re 21. And then I think Miguel said, ‘You ought to come out to Hollywood, be an actor.’ And I was like, okay. I had an old beat-up Monte Carlo, it was running on about four cylinders, and I bought a case of oil and sort of nursed it from Kentucky to Los Angeles. I pulled up in the driveway of my Aunt Rosemary’s house in Beverly Hills, this very rich place, and my car had rust all over it.”

On success and his aunt, Rosemary Clooney “My aunt Rosemary was a great jazz singer. I asked her, ‘Why are you a better singer now when you’re 70 years old and you can’t hold a note?’ And she goes, ‘Because I don’t have to prove I can sing anymore. Just serve the music, just serve the material.’ I’m leaning toward that [philosophy] more and more—in my career, in life.

“Handling success well is a trick. I’ve got a great advantage because my aunt Rosemary was very successful at a very young age in the ’50s, and she didn’t handle it well. She paid a very heavy price for it for a long period of time—probably about 20 years, she sort of dropped off the face of the earth. And then she came back roaring and was great. But she had a tough time of it. So I got a really good lesson in the idea that all of this is fleeting. Anyone who thinks that success is a permanent state, particularly in my line of work, is just an idiot. I know what the journey is, and I want to try and enjoy it while I can.” On his father influencing him to be a storyteller “I grew up around a storyteller, my father. When you come out of the radio age, where you didn’t even have moving pictures, people all told great stories and were really good at it. There’s an art to it that’s dying, because now you can just watch TV or text message and not even spell the words out. The worst crime you could do in my family was tell a boring story. If I did that my father would go, ‘Here’s an idea, George, next time you tell a story have a point to it.’ He’d just bury me [Laughs].”

On the appeal of The Ides of March outside America “Everywhere it’s played, they think it’s got something to do with their politics. When I had to pitch this movie, I would say, ‘Okay, here’s why it’s universal and not just an American film about delegate counts.’ I pitched the idea of a morality tale. I often referenced ER, because when we first finished the pilot the network thought no one was going to get it. They thought no one would understand words like supraventricular tachyarrhythmia. But the characters were what sold it—that’s what people cared about.”

On the other fall film he stars in, The Descendants (in theaters Nov. 18) “It’s by a wonderful director named Alexander Payne [Election, About Schmidt, Sideways]. He’s the real deal, somebody that I greatly admire as a director and as a man. It’s a very funny, very sad movie about a man trying to come to terms with some mistakes he’s made over his life, including not really paying attention to his kids. It deals with some tough issues, but it’s got humor in it. What a boring day it would be without humor.”